Diethyl (4-butoxy-3-methoxybenzylidene)malonate | 121174-60-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: Diethyl (4-butoxy-3-methoxybenzylidene)malonate
• 英文别名: diethyl 4'-n-butoxy-3'-methoxybenzalmalonate；Diethyl 2-[(4-butoxy-3-methoxyphenyl)methylidene]propanedioate
• CAS: 121174-60-5
• 化学式: C₁₉H₂₆O₆
• 分子量: 350.412
• InChiKey: IDCDUGXPZVLMCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Diethyl (4-butoxy-3-methoxybenzylidene)malonate 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 甲醇 、 水 为溶剂， 60.0 ℃ 、275.79 kPa 条件下， 反应 19.0h， 生成
  参考文献：
  名称：

  Inhibition of cyclic adenosine-3',5'-monophosphate phosphodiesterase from vascular smooth muscle by rolipram analogs

  摘要：

  Rolipram [(R,S)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidone] has been shown to inhibit selectively the cAMP phosphodiesterase (PDE) of vascular smooth muscle. In order to further explore the structural requirements for selective PDE inhibition, we synthesized a series of rolipram derivatives differently substituted either at the pyrrolidinone or at the aromatic ring. Among these compounds, rolipram was the most active compound. Semirigid analogues were prepared and used for an evaluation of the active conformation of rolipram. Structural comparison with two other potent and chemically different smooth muscle cAMP-PDE inhibitors, trequinsin and Ro 20-1724, allows us to propose a first topological model of the smooth muscle cAMP-PDE pharmacophore.

  DOI：

  10.1021/jm00127a009

文献信息

• Compositions comprenant un dérivé de dibenzoylméthane, un dérivé de 1;3.5-triazine et un benzalmalonate de diakyle et utilisations
  申请人：L'OREAL

  公开号：EP0848947B1

  公开（公告）日：1999-08-11
• US5624663A
  申请人：——

  公开号：US5624663A

  公开（公告）日：1997-04-29
• US5670140A
  申请人：——

  公开号：US5670140A

  公开（公告）日：1997-09-23
• US5882634A
  申请人：——

  公开号：US5882634A

  公开（公告）日：1999-03-16
• Inhibition of cyclic adenosine-3',5'-monophosphate phosphodiesterase from vascular smooth muscle by rolipram analogs
  作者：Michel C. Marivet、Jean Jacques Bourguignon、Claire Lugnier、Andre Mann、Jean Claude Stoclet、Camille Georges Wermuth

  DOI：10.1021/jm00127a009

  日期：1989.7

  Rolipram [(R,S)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidone] has been shown to inhibit selectively the cAMP phosphodiesterase (PDE) of vascular smooth muscle. In order to further explore the structural requirements for selective PDE inhibition, we synthesized a series of rolipram derivatives differently substituted either at the pyrrolidinone or at the aromatic ring. Among these compounds, rolipram was the most active compound. Semirigid analogues were prepared and used for an evaluation of the active conformation of rolipram. Structural comparison with two other potent and chemically different smooth muscle cAMP-PDE inhibitors, trequinsin and Ro 20-1724, allows us to propose a first topological model of the smooth muscle cAMP-PDE pharmacophore.